1,4-dideoxy-1,4-imino-D-glucitol hydrochloride | 109122-01-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1,4-dideoxy-1,4-imino-D-glucitol hydrochloride
• 英文别名: (2R,3S,4S)-2-[(1S)-1,2-dihydroxyethyl]pyrrolidine-3,4-diol;hydrochloride
• CAS: 109122-01-2
• 化学式: C₆H₁₃NO₄*ClH
• 分子量: 199.634
• InChiKey: IFRNNJQXHHLGKS-BTVCFUMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.99
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  97.5
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3,5,6-tetra-O-benzyl-D-galactofuranose 在 palladium on activated charcoal 、 cobalt(II) chloride 吡啶 、 盐酸 、 sodium tetrahydroborate 、 盐酸羟胺 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 36.0h， 生成 1,4-dideoxy-1,4-imino-D-glucitol hydrochloride
  参考文献：
  名称：

  Buchanan, J. Grant; Lumbard, Keith W.; Sturgeon, Robert J., Journal of the Chemical Society. Perkin transactions I, 1990, p. 699 - 706

  摘要：

  DOI：

文献信息

• A short, versatile approach to polyhydroxylated pyrrolidines utilizing a reductive elimination-reductive amination as a key step
  作者：Ronald C Bernotas

  DOI：10.1016/0040-4039(90)87010-w

  日期：1990.1

  An efficient synthesis of epimeric alpha-vinyl pyrrolidines starting from methyl 4,6--benzylidene gluco- and galactopyranosides gave ready access to hydroxylated pyrrolidines.

  由甲基4，6-亚苄基葡萄糖和吡喃半乳糖苷开始的高效异构体α-乙烯基吡咯烷酮的合成容易获得羟基化的吡咯烷酮。
• Asymmetric routes toward polyhydroxylated pyrrolidines: Synthesis of 1,4-dideoxy-1,4-imino-d-galactitol and 1,4-dideoxy-1,4-imino-d-glucitol
  作者：Giuliana Righi、Emanuela Mandic'、Carla Sappino、Ergys Dema、Paolo Bovicelli

  DOI：10.1016/j.carres.2016.09.018

  日期：2016.11

  Herein the total synthesis of the pyrrolidine alkaloids 1,4-dideoxy-1,4-imino-d-galactitol and its diastereoisomer 1,4-dideoxy-1,4-imino-d-glucitol is described, starting from a common optically active precursor. The key step in our approach was the double diastereoselection in the asymmetric dihydroxylation of chiral vinyl azido alcohols, obtained by means of two different regio- and stereoselective

  本文描述了从常见的旋光活性开始的吡咯烷生物碱1,4-二脱氧-1,4-亚氨基-d-半乳糖醇及其非对映异构体1,4-二脱氧-1,4-亚氨基-d-葡萄糖醇的全合成前体。我们方法的关键步骤是手性乙烯基叠氮基醇的不对称二羟基化中的双非对映异构，这是通过相应手性乙烯基环氧化物的两个不同的区域和立体选择性亲核开口获得的。
• A New Access to Polyhydroxylated Pyrrolidines from Epoxyaldehydes
  作者：Tahar Ayad、Yves Génisson、Michel Baltas、Liliane Gorrichon

  DOI：10.1055/s-2001-14593

  日期：——

  Our approach relies on the stereocontrolled vinylation of a chiral α,β-epoxyimine derived from the corresponding aldehyde. Regioselective opening of the oxirane with carbonate anion allowed the formation of an oxazolidinone intermediate from which the glucosidase inhibitor 1,4-dideoxy-1,4-imino-d-glucitol (14) was synthesised. Direct cyclisation into a 2-vinyl-3,4-epoxypyrrolidine afforded a valuable intermediate for the preparation of synthetic azasugar analogues.

  我们的方法依赖于从相应的醛中衍生出的手性δ±,δ²-环氧亚胺的立体控制乙烯基化。用碳酸阴离子对环氧乙烷进行区域选择性开环，可形成恶唑烷酮中间体，并由此合成出葡萄糖苷酶抑制剂 1,4-二脱氧-1,4-亚氨基-d-葡萄糖醇 (14)。直接环化成 2-乙烯基-3,4-环氧吡咯烷后，就得到了制备合成氮杂糖类似物的重要中间体。
• Synthesis of 1,4-dideoxy-1,4-imino-d-glucitol, a glucosidase inhibitor
  作者：Janos Kuszmann、László Kiss

  DOI：10.1016/s0008-6215(00)90194-0

  日期：1986.9

  and 4,5-anhydro derivatives. Reduction of this mixture by transfer hydrogenation using ammonium formate in methanol and Pd/C as catalyst afforded 1,4-dideoxy-1,4-imino-D-glucitol (4), the structure of which was proved after acetylation by 1H-n.m.r. spectroscopy. Compound 4 is a potent alpha-D-glucosidase inhibitor (Ki 7 X 10(-4)M) and a less potent beta-D-glucosidase inhibitor (Ki 1.25 X 10(-4)M), and

  1,2：5,6-二-O-异亚丙基-D-葡萄糖醇通过其1,4-二甲磺酸盐转化为1-叠氮基-4-甲磺酸盐，在脱保护并用氢氧化钡处理后，得到9：1的糖基。相应的3，4-和4，5-脱水衍生物的混合物。通过在甲醇中以甲酸铵和Pd / C为催化剂的转移氢化反应来还原该混合物，得到1,4-二脱氧-1,4-亚氨基-D-葡萄糖醇（4），其结构经1H-nmr乙酰化后证明光谱学。化合物4是有效的α-D-葡糖苷酶抑制剂（Ki 7 X 10（-4）M）和次要的β-D-葡糖苷酶抑制剂（Ki 1.25 X 10（-4）M），并抑制β-D-半乳糖苷酶非竞争性。
• BUCHANAN, J. GRANT;LUMBARD, KEITH W.;STURGEON, ROBERT J.;THOMPSON, DERYK +, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 699-706
  作者：BUCHANAN, J. GRANT、LUMBARD, KEITH W.、STURGEON, ROBERT J.、THOMPSON, DERYK +

  DOI：——

  日期：——